I don't see any connection between this post and DFW's address, nor do I understand why this would be depressing.
But there's still nothing glamorous about not having enough money to cover basic expenses, unexpected emergencies, to live in a comfortable place, to be able to afford the transportation that will get you to your passions.
I would not be worse off if I had abandoned some of my dreams a little earlier and pursued money for a little while longer.
Achievement does NOT necessarily require playing a nasty, zero-sum competitive game.
Note: I could give a shit about getting into an elite school (I have 1 semester at UIC, and nothing else), and a hack to do that wasn't my takeaway from the post.